Fritz hansgirg



rmrz 'nnnseme, or cm'i'rz, STYRIA, Ausrnm.

ART OF MANUFACTURING PERYLEN.

No Drawing.

To all iv i'wm it may concern: Be it known that I, FRITZ HANSGIRG,residing at Gratz, in Styria, Austria, have invented new and usefulImprovements in the Art of Manufacturing Perylen, for which I have filedapalications in Austria Feb. 28, 1918, and in ermany March 9, 1918,- ofwhich the following is a specification.-

The present synthetic methods of manu facturing perylen starting with a,oz-dinaphtyl or its derivatives give but small yields of perylen.

I have found that a high yield of perylen may be obtained by treatingthe fi-derivatives of naphthalene or of a, oz-dinapthyk withhalogenizing agents such as the halogen compounds of phosphorus,antimony, arsenic, aluminium and others, whereby (i-su-bstituted halogenderivatives of naphthalene or of oz, oz-dinaphtyl result, and these haloen. derivatives are then transformed into pery en in a known manner bymeans of ring closing agents, such as chlorid of aluminium, or by meansof pyrogene synthesis. It is advantageous to use in the process areducing flux, such as phosphorous acid. The reaction may be earned outin such a way that starting with [i-substituted derivatives ofnaphthalene or of a, oz-dinaphtyl, the fi-substituted halogenderivatives of this hydrocarbon are obtained and transformed in oneoperation with or without the isolation of the halogen derivatives. Itis also possible to start directly with (i-halogen-oa, or-dinaphtylswhich may be obtained in any known and convenient The following givesome examples of the methods of procedure:

(1) 1 kilogram B-dinaphthol is quickly heated to 500 degrees centigradewith 1 kilogram phosphorous acid while adding 1kg. phosphorustrichlorid. The reaction takes 1 place with heavy foaming while phosphinescapes. and ignites as it passes off. When the formation of hydrogenphosphid gas ceases, the'product of the reaction is fractionallydistilled and thereby separated from the a, a dinaphtyl oxid which alsoforms in the reaction. The yield is of the starting material and iscalled technically pure perylen, and after crystallizing the technicalproduct out of benzol or concentrated acetic acid, analysis shows thatpure perylen is obp tained, the yield being 80% of the technically pureperylen which was used; (2) 'Bystarting with, fi-fi-dichlor-a, a-di-Application filed July so,

.tions as Specification of Letters Patent. Pate t d J l 12 192 I919.Serial no. 314,388.

naphtyl the. reaction may be carried out with the mentioned flux orwithout it. If the reaction is carried out without using a flux then asmaller yield results.

(a). 1 kg. fi-(i-dichlor-a, a-dinaphtyl is heatedtobetween500 and 600centigrade and' the. product of't he reaction is treated as explainedin' exampleNo. 1. The yield is 20% of the starting material intechnically pure perylen.

-- (b),-1 kg. (i-fi-dichlor-a, o z-dinaphtyl is heated with 1 kg.phosphorous acid to: 500 degrees centigrade and the product of react1onis treatedas in No. 1. A yield of 75% of the. starting material isobtained in technlcally ure perylen.

(3) y carrylng out the operation as described in example No. 1 andheating a mixture of the substances in the same proporgiven in thatexample, but terminating the eating before the evolution of hydrogen.phosphid gas ceases, and then letting the product of reaction cool downwithout distilling it, it is possibleby boiling the cooled residue withsodium or caustic potashto isolate a dark colored amorphous substancewhich can not be crystallized and therefore can not be identified. Thissubstance is transformed into perylen by heatexamples given aboveinstead of the chlorin' compounds the corresponding compounds of theother'halogens can be used and, in the place of phosphorous acid, theother acids of phosphorus.

Having now described my invention what I claim as new and ask to secureby Letters Patent is 1. A method of manufacturing perylen, consisting inadding a fi-substituted derivative of a naphthalene nucleus to ahalogenizing agent, and heating the product of the reaction.

2. A method of manufacturing perylen, consisting in adding a(l-substituted derivative of a naphthalene nucleus to a halogenizingagent, and subjecting the product of the reaction to heat in thepresence'of a phoshorous acid to transform it into perylen.

A method of manufacturing perylen, consisting in adding a (l-substitutedderivative of a naphthalene nucleus to a halogeniZ- ing agent, andsubjecting the product of the reaction to heat in the presence of aphosphorous acid and a ring-closing agent to transform it into perylen.

4. A method of manufacturing perylen, consisting in adding afi-substituted derivative of the a, a-dinaphtyl to a halogenizing agent,and heating the product of the reaction.

5. A method of manufacturing perylen, consisting in adding a(fi-substituted derivative of the a, a-dinaphtyl to a halogenizingagent, and heating the product of the reaction in the presence of aphosphorous acid 15 to transform it into perylen.

.phosphid gas ceases, isolating the product of the reaction, and heatingsaid product in the presence of aluminum chlorid to transform it intoperylen.

In testimony whereofI aflix my signature in the presence of twosubscribin witnesses.

DR. FRITZ HA SGIRG. Witnesses:

Dr. DIEGO LASTRAS, LEOP. LAHN.

